Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence

Jayaram, Vankudoth; Sridhar, Tailor; Sharma, G. V. M.; Berrée, Fabienne; Carboni, Bertrand

doi:10.1021/acs.joc.7b02831

Cited by 24 publications

(10 citation statements)

References 60 publications

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“…Carboni and coworkers reported several studies using alkenyl boronic esters or 1,2-diboronic esters for the synthesis of functionalized heterocycles. − A PR using 1-alkene-1,2-diboronic esters was reported in a PR–Suzuki coupling sequence. The Petasis product obtained from ( Z )-1-alkene-1,2-diboronic esters, secondary amines, and glyoxylic acid was directly esterified to form the product ( E )-γ-boronated amino esters 267 by treating with diazomethane solution in diethyl ether.…”

Section: Petasis Cascade and Sequence Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

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Section: Petasis Cascade and Sequence Reactionsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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“…( 1)]. To showcase the utility of aalkenyl boronates, 3 a could be converted into alkenyl azide [15] [Eq. (2)] or 1,1-diaryl olefins [1] [Eq.…”

Section: Angewandte Chemiementioning

confidence: 99%

Cobalt‐Catalyzed Markovnikov‐Type Selective Hydroboration of Terminal Alkynes

Chen

Shen

2020

Angewandte Chemie

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A cobalt-catalyzed Markovnikov-type hydroboration of terminal alkynes with HBpin to access a-alkenyl boronates with good regioselectivity and atom economy is reported. A new ligand has been developed for the cobalt hydride catalyst that has been used for a unique Markovnikov selective insertion of terminal alkynes into metal hydride bond. This operationally simple protocol exhibits excellent functional group tolerance to deliver valuable alkene derivatives. Scheme 1. Metal-catalyzed selective hydroboration of terminal alkynes.

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“…The existing synthetic approaches to 1-isoquinolones 2 encompass annulation of benzonitrile to N -methyl 2-toluamides 1 , facilitated by n -BuLi (2 equiv), Pd-catalyzed cyclization of o -alkynyl Weinreb benzamide, Cu-catalyzed annulation of propiolic acids RCCCO 2 H to 2-BrC 6 H 4 CO 2 H, Ag-catalyzed annulation of 1-alkynyl-2-triazolylbenzene derivatives, Pd(II)- or Ni(II)-catalyzed addition of arylboronic acids ArB(OH) 2 to methyl 2-(cyanomethyl)benzoate 2-(MeO 2 C)C 6 H 4 CH 2 CN, and other methods. , …”

Section: Resultsmentioning

confidence: 99%